Compound and light-emitting device including the same

ABSTRACT

A compound of Formula 1, as disclosed herein, is useful in an organic light emitting device and apparatuses including the same.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit of Korean PatentApplication No. 10-2019-0134798, filed on Oct. 28, 2019, which is herebyincorporated by reference for all purposes as if fully set forth herein.

BACKGROUND Field

Exemplary implementations of the invention relate generally to acompound and, more particularly, to a compound useful in an organiclight emitting device and apparatuses including the same.

Discussion of the Background

Organic light-emitting devices are self-emission devices that have wideviewing angles, high contrast ratios, short response times, andexcellent characteristics in terms of brightness, driving voltage, andresponse speed, compared to devices in the art.

An example of the organic light-emitting device may include a firstelectrode disposed on a substrate, and a hole transport region, anemission layer, an electron transport region, and a second electrode,which are sequentially disposed on the first electrode. Holes providedfrom the first electrode may move toward the emission layer through thehole transport region, and electrons provided from the second electrodemay move toward the emission layer through the electron transportregion. Carriers, such as holes and electrons, recombine in the emissionlayer to produce excitons. These excitons transit from an excited stateto a ground state, thereby generating light.

The above information disclosed in this Background section is only forunderstanding of the background of the inventive concepts, and,therefore, it may contain information that does not constitute priorart.

SUMMARY

Applicant realized that many existing organic light-emitting devicessuffer from luminescent inefficiencies.

Compounds for organic light-emitting devices and apparatuses includingthe same made according to the principles and exemplary implementationsof the invention provide a luminescent material having better efficiencycharacteristics than known compounds.

For example, the compound of Formula 1 according to some exemplaryembodiments of the invention is structurally distinct by furtheractivating multiple resonance and has a high f value and a lowerΔE_(ST). Thus, when an emission layer of an organic light-emittingdevice includes the compound of Formula 1 according to at least oneexemplary embodiment, efficiency is increased. The compound of Formula 1according to some exemplary embodiments functions as a delayedfluorescence dopant.

Additional features of the inventive concepts will be set forth in thedescription which follows, and in part will be apparent from thedescription, or may be learned by practice of the inventive concepts.

According to one aspect of the invention, light-emitting deviceincludes: a first electrode; a second electrode facing the firstelectrode; and an intermediate layer disposed between the firstelectrode and the second electrode and comprising an emission layer,wherein the first electrode and the second electrode each independentlyinclude at least one selected from lithium (Li), silver (Ag), magnesium(Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), indium tin oxide(ITO), zinc oxide (ZnO), tin oxide (SnO2) and indium zinc oxide (IZO),and the intermediate layer comprises the compound of Formula 1:

wherein, in Formula 1:

Y is O, S, or Se;

X₁ is NR₁₁, O, or S, X₂ is NR₁₂, O, or S, X₃ is NR₁₃, O, or S, and X₄ isNR₁₄, O, or S;

l, m, n, and o are each, independently from one another, 0 or 1, and atleast one of l, m, n, and o is 1;

R₁ to R₅ and R₁₁ to R₁₄ are each, independently from one another,hydrogen, deuterium, a substituted or unsubstituted C₁-C₆₀ alkyl group,a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic fused polycyclic group, asubstituted or unsubstituted monovalent non-aromatic fusedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —P(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂);

a1, a2, a3, and a5 are each, independently from one another, 1, 2, or 3;

a4 is 1 or 2;

two neighboring substituents of R₁ to R₅ and R₁₁ to R₁₄ are linked toeach other to form a ring, and

at least one substituent of the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic fusedpolycyclic group, and the substituted monovalent non-aromatic fusedheteropolycyclic group is:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each, independently from one another, substitutedwith at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic fused polycyclicgroup, a monovalent non-aromatic fused heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂); and

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic fused polycyclic group, or amonovalent non-aromatic fused heteropolycyclic group, each,independently from one another, optionally substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic fused polycyclic group, a monovalent non-aromatic fusedheteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—C(═P)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂);

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each,independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic fused polycyclic group, amonovalent non-aromatic fused heteropolycyclic group, a biphenyl group,or a terphenyl group.

The variables l and m may be 1.

The variables l, m, and o may be 1, and n may be 0, or l, m, and n maybe 1, and o may be 0.

The variables l, m, n, and o may be 1.

The variable Y may be O, and R₁ to R₅ and R₁₁ to R₁₄ may each,independently from one another, be a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic fused polycyclic, or —N(Q₁)(Q₂),with Q₁ and Q₂ defined herein.

The variables R₁₁ to R₁₄ may each, independently from one another, be asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, or a substituted or unsubstitutedmonovalent non-aromatic fused polycyclic.

The variables R₁₁ to R₁₄ may each, independently from one another, bevarious groups and their substituents as defined herein.

The variables R₁ to R₅ and R₁₁ to R₁₄ may each, independently from oneanother, be hydrogen, deuterium, a methyl group, an ethyl group, apropyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, apentyl group, an iso-amyl group, or a hexyl group, or a group of Formula2a or 2b, as defined herein.

The compound of Formula 1 may be a compound of Formula 2 or 3, asdefined herein.

The compound of Formula 1 may be a compound of Formula 4 or 5, asdefined herein.

The compound of Formula 1 may be a compound of Formula 6 or 7, asdefined herein.

The compound of Formula 1 may be one of the compounds of the chemicalstructures 1-96, as defined herein.

The first electrode may include an anode, the second electrode mayinclude a cathode, and the intermediate layer may include: i) a holetransport region disposed between the first electrode and the emissionlayer and including a hole injection layer, a hole transport layer, anemission auxiliary layer, an electron blocking layer, or any combinationthereof; and ii) an electron transport region disposed between theemission layer and the second electrode and including a hole blockinglayer, an electron transport layer, an electron injection layer, or anycombination thereof.

The emission layer may include the compound of Formula 1, as definedherein.

The emission layer may include a fluorescent emission layer.

The emission layer may include a dopant, and the dopant may include thecompound of Formula 1, as defined herein.

The compound may include a delayed fluorescence dopant of Formula 1, asdefined herein.

The emission layer may include a blue emission layer.

An electronic apparatus may include a thin-film transistor and alight-emitting device including: a first electrode; a second electrodefacing the first electrode; and an intermediate layer disposed betweenthe first electrode and the second electrode and including an emissionlayer, wherein the intermediate layer comprises the compound of claim 1,and

wherein the thin-film transistor may include a source electrode, a drainelectrode, an activation layer, and a gate electrode, and the firstelectrode of the light-emitting device may be electrically connected toone of the source electrode and the drain electrode of the thin-filmtransistor.

It is to be understood that both the foregoing general description andthe following detailed description are exemplary and explanatory and areintended to provide further explanation of the invention as claimed.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings, which are included to provide a furtherunderstanding of the invention and are incorporated in and constitute apart of this specification, illustrate exemplary embodiments of theinvention, and together with the description serve to explain theinventive concepts.

FIG. 1 is a schematic cross-sectional diagram of an exemplary embodimentof an organic light-emitting device constructed according to principlesof the invention.

DETAILED DESCRIPTION

In the following description, for the purposes of explanation, numerousspecific details are set forth in order to provide a thoroughunderstanding of various exemplary embodiments or implementations of theinvention. As used herein “embodiments” and “implementations” areinterchangeable words that are non-limiting examples of devices ormethods employing one or more of the inventive concepts disclosedherein. It is apparent, however, that various exemplary embodiments maybe practiced without these specific details or with one or moreequivalent arrangements. In other instances, well-known structures anddevices are shown in block diagram form in order to avoid unnecessarilyobscuring various exemplary embodiments. Further, various exemplaryembodiments may be different, but do not have to be exclusive. Forexample, specific shapes, configurations, and characteristics of anexemplary embodiment may be used or implemented in another exemplaryembodiment without departing from the inventive concepts.

Unless otherwise specified, the illustrated exemplary embodiments are tobe understood as providing exemplary features of varying detail of someways in which the inventive concepts may be implemented in practice.Therefore, unless otherwise specified, the features, components,modules, layers, films, panels, regions, and/or aspects, etc.(hereinafter individually or collectively referred to as “elements”), ofthe various embodiments may be otherwise combined, separated,interchanged, and/or rearranged without departing from the inventiveconcepts.

The use of cross-hatching and/or shading in the accompanying drawings isgenerally provided to clarify boundaries between adjacent elements. Assuch, neither the presence nor the absence of cross-hatching or shadingconveys or indicates any preference or requirement for particularmaterials, material properties, dimensions, proportions, commonalitiesbetween illustrated elements, and/or any other characteristic,attribute, property, etc., of the elements, unless specified. Further,in the accompanying drawings, the size and relative sizes of elementsmay be exaggerated for clarity and/or descriptive purposes. When anexemplary embodiment may be implemented differently, a specific processorder may be performed differently from the described order. Forexample, two consecutively described processes may be performedsubstantially at the same time or performed in an order opposite to thedescribed order. Also, like reference numerals denote like elements.

When an element, such as a layer, is referred to as being “on,”“connected to,” or “coupled to” another element or layer, it may bedirectly on, connected to, or coupled to the other element or layer orintervening elements or layers may be present. When, however, an elementor layer is referred to as being “directly on,” “directly connected to,”or “directly coupled to” another element or layer, there are nointervening elements or layers present. To this end, the term“connected” may refer to physical, electrical, and/or fluid connection,with or without intervening elements. Further, the D1-axis, the D2-axis,and the D3-axis are not limited to three axes of a rectangularcoordinate system, such as the x, y, and z-axes, and may be interpretedin a broader sense. For example, the D1-axis, the D2-axis, and theD3-axis may be perpendicular to one another, or may represent differentdirections that are not perpendicular to one another. For the purposesof this disclosure, “at least one of X, Y, and Z” and “at least oneselected from the group consisting of X, Y, and Z” may be construed as Xonly, Y only, Z only, or any combination of two or more of X, Y, and Z,such as, for instance, XYZ, XYY, YZ, and ZZ. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items.

Although the terms “first,” “second,” etc. may be used herein todescribe various types of elements, these elements should not be limitedby these terms. These terms are used to distinguish one element fromanother element. Thus, a first element discussed below could be termed asecond element without departing from the teachings of the disclosure.

Spatially relative terms, such as “beneath,” “below,” “under,” “lower,”“above,” “upper,” “over,” “higher,” “side” (e.g., as in “sidewall”), andthe like, may be used herein for descriptive purposes, and, thereby, todescribe one elements relationship to another element(s) as illustratedin the drawings. Spatially relative terms are intended to encompassdifferent orientations of an apparatus in use, operation, and/ormanufacture in addition to the orientation depicted in the drawings. Forexample, if the apparatus in the drawings is turned over, elementsdescribed as “below” or “beneath” other elements or features would thenbe oriented “above” the other elements or features. Thus, the exemplaryterm “below” can encompass both an orientation of above and below.Furthermore, the apparatus may be otherwise oriented (e.g., rotated 90degrees or at other orientations), and, as such, the spatially relativedescriptors used herein interpreted accordingly.

The terminology used herein is for the purpose of describing particularembodiments and is not intended to be limiting. As used herein, thesingular forms, “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise. Moreover,the terms “comprises,” “comprising,” “includes,” and/or “including,”when used in this specification, specify the presence of statedfeatures, integers, steps, operations, elements, components, and/orgroups thereof, but do not preclude the presence or addition of one ormore other features, integers, steps, operations, elements, components,and/or groups thereof. It is also noted that, as used herein, the terms“substantially,” “about,” and other similar terms, are used as terms ofapproximation and not as terms of degree, and, as such, are utilized toaccount for inherent deviations in measured, calculated, and/or providedvalues that would be recognized by one of ordinary skill in the art.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this disclosure is a part. Terms,such as those defined in commonly used dictionaries, should beinterpreted as having a meaning that is consistent with their meaning inthe context of the relevant art and should not be interpreted in anidealized or overly formal sense, unless expressly so defined herein.

A di aza boran naphtho anthracene (DABNA) based thermally activateddelayed fluorescence (TADF) compound of the related art has TADFcharacteristics by separating highest occupied molecular orbital (HOMO)and lowest unoccupied molecular orbital (LUMO) by multiple resonancebetween an N atom and a B atom, has high luminescence efficiency due toa large overlap between HOMO and LUMO, and has a small full width at thehalf maximum (FWHM) and stokes shift due to a small change in thestructure before and after transition.

However, due to a relatively large ΔE_(ST) value, an exciton lifetime(Tau) value is large, resulting in large roll-off under a high currentdensity load.

The addition of a boron atom results in a “short-range charge transfer(CT)” phenomenon that further increases HOMO/LUMO separation in whichintersecting atoms are separated from each other. When the molecularplane is fused widely, delocalization may be enlarged and polarizabilitymay be increased, thereby further increasing an f value, resulting inhigh efficiency in device manufacturing.

A compound represented by Formula 1 according to an aspect is asfollows.

In Formula 1,

Y may be O, S, or Se,

X₁ may be NR₁₁, O, or S, X₂ may be NR₁₂, O, or S, X₃ may be NR₁₃, O, orS, and X₄ may be NR₁₄, O, or S,

l, m, n, and o may each independently be 0 or 1, and at least one of l,m, n, and o may be 1,

R₁ to R₅ and R₁₁ to R₁₄ may each independently be selected fromhydrogen, deuterium, a substituted or unsubstituted C₁-C₆₀ alkyl group,a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —P(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

a1, a2, a3, and a5 may each independently be an integer from 1 to 3,

a4 may be 1 or 2,

two neighboring substituents of R₁ to R₅ and R₁₁ to R₁₄ may be linked toeach other to form a ring, and

at least one substituent of the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and—P(═O)(Q₃₁)(Q₃₂),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may eachindependently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

Formula 1 according to an exemplary embodiment includes one or moreboron atom compared to the DABNA-based compound having one boron of therelated art. Also, molecular plane is widely fused and thedelocalization is enlarged such that polarizability is increased and anf value is further increased. Also, due to a linker Y as a hetero atomat the center (especially, when Y is O), the delocalization is furtherexpanded and the multiple resonance becomes greater.

In one or more exemplary embodiments, a compound of Formula 1 may havean f value of about 0.3 to about 0.8.

In one or more exemplary embodiments, when a1 is 2 or more, a pluralityof R₁(s) may be equal to or different from each other, and adjacentR₁(s) may be connected to each other to form a ring. When a2 is 2 ormore, a plurality of R₂(s) may be equal to or different from each other,and adjacent R₂(s) may be connected to each other to form a ring. Whena3 is 2 or more, a plurality of R₃(s) may be equal to or different fromeach other, and adjacent R₃(s) may be connected to each other to form aring. When a4 is 2 or more, a plurality of R₄(s) may be equal to ordifferent from each other, and adjacent R₄(s) may be connected to eachother to form a ring. When a5 is 2 or more, a plurality of R₅(s) may beequal to or different from each other, and adjacent R₅(s) may beconnected to each other to form a ring. In one or more exemplaryembodiments, the plurality of R₁(s) is connected to each other to form acarbazole.

In one or more exemplary embodiments, in Formula 1, each of I and m maybe 1.

In one or more exemplary embodiments, in Formula 1, at least one of Iand o may be 1, and at least one of m and n may be 1.

In one or more exemplary embodiments, in Formula 1, Y may be O, each ofI and m may be 1, X₁ may be NR₁₁ or O, and X₂ may be NR₁₂ or O.

In one or more exemplary embodiments, in Formula 1, I, m, and o may be1, and n may be 0, or l, m, and n may be 1, and o may be 0.

In one or more exemplary embodiments, in Formula 1, Y may be O, I, m,and o may be 1, n may be 0, X₁ may be NR₁₁ or O, X₂ may be NR₁₂ or O,and X₄ may be NR₁₄ or O, or

l, m, and n may be 1, o may be 0, X₁ may be NR₁₁ or O, X₂ may be NR₁₂ orO, and X₃ may be NR₁₃ or O.

In one or more exemplary embodiments, in Formula 1, each of l, m, n, ando may be 1.

In one or more exemplary embodiments, in Formula 1, each of l, m, n, ando may be 1, X₁ may be NR₁₁ or O, X₂ may be NR₁₂ or O, X₃ may be NR₁₃ orO, and X₄ may be NR₁₄ or O.

In one or more exemplary embodiments, Y may be O, and R₁ to R₅ and R₁₁to R₁₄ may each independently be selected from a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic, and —N(Q₁)(Q₂).

In one or more exemplary embodiments, R₁₁ to R₁₄ may each independentlybe a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, or a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic.

In one or more exemplary embodiments, R₁₁ to R₁₄ may each independentlybe selected from: a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a thiadiazolyl group, an oxadiazolyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, and an azacarbazolyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a thiadiazolyl group, an oxadiazolyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂).

In one or more exemplary embodiments, R₁ to R₅ and R₁₁ to R₁₄ may eachindependently be selected from hydrogen, deuterium, a methyl group, anethyl group, a propyl group, an isobutyl group, a sec-butyl group, ater-butyl group, a pentyl group, an iso-amyl group, a hexyl group, andFormulae 2a to 2b:

In Formulae 2a to 2b, Z₁ to Z₃ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a thiadiazolyl group, an oxadiazolyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, and an azacarbazolyl group,

a33 may be an integer from 1 to 5, and

* indicates a binding site to neighboring atom.

In one or more exemplary embodiments, Formula 1 may be represented byFormula 2 or 3:

In Formulae 2 and 3, R₁ to R₅, X₁, X₂, and a1 to a5 are the same asdescribed in connection with Formula 1.

In one or more exemplary embodiments, Formula 1 may be represented byFormula 4 or 5:

In Formulae 4 and 5, R₁ to R₅, X₁, X₂, X₄, and a1 to a5 are the same asdescribed in connection with Formula 1.

In one or more exemplary embodiments, Formula 1 may be represented byFormula 6 or 7:

In Formulae 6 and 7, R₁ to R₅, X₁ to X₄, and a1 to a5 are the same asdescribed in connection with Formula 1.

In one or more exemplary embodiments, a compound represented by Formula1 may be any one of compounds below:

The expression “(an intermediate layer) includes at least one of thecompounds” used herein may include an intermediate layer havingidentical or two or more different compounds represented by Formula 1.

In one or more exemplary embodiments, the intermediate layer mayinclude, as the compound, only Compound 1. In this regard, Compound 1may exist in the emission layer of the light-emitting device. In one ormore exemplary embodiments, the intermediate layer may include, as thecompound, Compound 1 and Compound 2. Compound 1 and Compound 2 may existin an identical layer (for example, Compound 1 and Compound 2 may allexist in an emission layer), or different layers (for example, Compound1 may exist in an emission layer and Compound 2 may exist in an electrontransport region).

According to one or more exemplary embodiments, provided is anlight-emitting device including:

a first electrode;

a second electrode facing the first electrode; and

an intermediate layer disposed between the first electrode and thesecond electrode and including an emission layer,

wherein the intermediate layer includes a compound of Formula 1. In oneor more exemplary embodiments, the light-emitting device may be anorganic light-emitting device.

According to one or more exemplary embodiments,

the first electrode of the light-emitting device may be an anode,

the second electrode of the light-emitting device may be a cathode, and

the intermediate layer further includes a hole transport regioninterposed between the first electrode and the emission layer and anelectron transport region interposed between the emission layer and thesecond electrode,

wherein the hole transport region may include a hole injection layer, ahole transport layer, an emission auxiliary layer, an electron blockinglayer, or any combination thereof, and

the electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

In one or more exemplary embodiments, the emission layer may be afluorescent emission layer.

In one or more exemplary embodiments, a compound of Formula 1 may beused in the emission layer.

In one or more exemplary embodiments, the emission layer may be afluorescent emission layer.

In one or more exemplary embodiments, the emission layer may include adopant, and the dopant may include the compound. In one or moreexemplary embodiments, the dopant may consist of the compound of Formula1.

In one or more exemplary embodiments, the compound may act as a delayedfluorescence dopant. In one or more exemplary embodiments, the compoundof Formula 1 may act as a delayed fluorescence dopant in the emissionlayer.

In one or more exemplary embodiments, the emission layer may be a blueemission layer.

An electronic apparatus according to one or more exemplary embodimentsincludes a thin-film transistor and the light-emitting device, whereinthe thin-film transistor includes a source electrode, a drain electrode,an activation layer, and a gate electrode, and the first electrode ofthe light-emitting device may be in electrical connection with one ofthe source electrode and the drain electrode of the thin-filmtransistor.

The term “intermediate layer” as used herein refers to a single layerand/or a plurality of layers interposed between the first electrode andthe second electrode of the light-emitting device. A material includedin the “intermediate layer” may be an organic material, inorganicmaterial, or any combination thereof.

Description of FIG. 1

FIG. 1 is a schematic cross-sectional diagram of an exemplary embodimentof an organic light-emitting device constructed according to principlesof the invention.

The light-emitting device 10 may include a first electrode 110, anintermediate layer 150, and a second electrode 190. The intermediatelayer 150 may include a hole transport region, an emission layer, and anelectron transport region, as described in detail below.

Hereinafter, the structure of the light-emitting device 10 according toan exemplary embodiment and an exemplary method of manufacturing thelight-emitting device 10 will be described in connection with FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally disposed under the firstelectrode 110 or above the second electrode 190. As the substrate, aglass substrate or a plastic substrate may be used.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming a first electrode 110 on the substrate. When thefirst electrode 110 is an anode, a high work function material foreasily injecting holes may be used as the material for forming the firstelectrode 110.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, an indium tin oxide (ITO), anindium zinc oxide (IZO), a tin oxide (SnO₂), a zinc oxide (ZnO), or anycombinations thereof may be used as a material for forming the firstelectrode 110, but the exemplary embodiments are not limited thereto. Inone or more exemplary embodiments, when the first electrode 110 is asemi-transmissive electrode or a reflective electrode, magnesium (Mg),silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combinationsthereof may be used as a material for forming a first electrode 110, butthe exemplary embodiments are not limited thereto.

The first electrode 110 may have a single layer structure consisting ofa single layer or a multi-layered structure including a plurality oflayers. In one or more exemplary embodiments, the first electrode 110may have a three-layered structure of ITO/Ag/ITO, but the structure ofthe first electrode 110 is not limited thereto.

Intermediate Layer 150

The intermediate layer 150 is disposed on the first electrode 110. Theintermediate layer 150 includes the emission layer.

The intermediate layer 150 may further include the hole transport regionbetween the first electrode 110 and the emission layer and the electrontransport region between the emission layer and the second electrode190. The emission layer may include a dopant, such as a fluorescentdopant, as hereinafter described.

The intermediate layer 150 may further include a metal-containingcompound such as an organometallic compound, and an organic materialsuch as a quantum dot, in addition to various organic materials.

Hole Transport Region in the Intermediate Layer 150

The hole transport region may have i) a single layer structureconsisting of a single layer consisting of a single material, ii) asingle layer structure consisting of a single layer including aplurality of different materials, or iii) a multi-layered structureincluding a plurality of layers including a plurality of differentmaterials.

The hole transport region may include a hole injection layer (HIL), ahole transport layer (HTL), an emission auxiliary layer, an electronblocking layer (EBL), or any combination thereof.

In one or more exemplary embodiments, the hole transport region may havea multi-layered structure having a hole injection layer/hole transportlayer, a hole injection layer/hole transport layer/emission auxiliarylayer, a hole injection layer/emission auxiliary layer, a hole transportlayer/emission auxiliary layer, or a hole injection layer/hole transportlayer/electron blocking layer, wherein for each structure, constitutinglayers are sequentially stacked from the first electrode 110 in thisstated order, but the structure of the hole transport region is notlimited thereto.

The hole transport region may include a compound represented by Formula201, a compound represented by Formula 202, or any combination thereof:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be a substituted or unsubstitutedC₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, or a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be *—O—*′, *—S—*′, *—N(Q₂₀₁)—*′, a substituted or unsubstitutedC₁-C₂₀ alkylene group, a substituted or unsubstituted C₂-C₂₀ alkenylenegroup, a substituted or unsubstituted C₃-C₁₀ cycloalkylene group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkylene group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, or a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be 0, 1, 2, or 3 (for example, 0, 1,or 2),

xa5 may be an integer from 1 to 10 (for example, 1, 2, 3, or 4), and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, or a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In one or more exemplary embodiments, in Formula 202, R₂₀₁ and R₂₀₂ mayoptionally be linked to each other via a single bond, adimethyl-methylene group, or a diphenyl-methylene group, and R₂₀₃ andR₂₀₄ may optionally be linked to each other via a single bond, adimethyl-methylene group, or a diphenyl-methylene group.

In one or more exemplary embodiments, i) at least one of R₂₀₁ to R₂₀₃ inFormula 201 and ii) at least one of R₂₀₁ to R₂₀₄ in Formula 202 may eachindependently be a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, an indenophenanthrenyl group, a pyridinyl group, apyrrole group, a thiophenyl group, a furanyl group, an indolyl group, abenzoindolyl group, an isoindolyl group, a benzoisoindolyl group, abenzosilolyl group, a benzothiophenyl group, a benzofuranyl group, acarbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, ora dibenzofuranyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group,a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a phenyl group substituted with a C₁-C₁₀ alkyl group, a phenyl groupsubstituted with —F, a naphthyl group, a phenanthrenyl group, an indenylgroup, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenylgroup, a spiro-bifluorenyl group, a benzofluorenyl group, adimethylbenzofluorenyl group, a diphenylbenzofluorenyl group, anindenophenanthrenyl group, a dimethylindenophenanthrenyl group, adiphenylindenophenanthrenyl group, a pyridinyl group, a pyrrolyl group,a thiophenyl group, a furanyl group, an indolyl group, a phenylindolylgroup, a benzoindolyl group, a phenylbenzoindolyl group, an isoindolylgroup, a phenylindolyl group, a benzoisoindolyl group, aphenylbenzoisoindolyl group, a benzosilolyl group, adimethylbenzosilolyl group, a diphenylbenzosilolyl group, abenzothiophenyl group, a benzofuranyl group, a carbazolyl group, aphenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzosilolylgroup, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, adibenzothiophenyl group, and a dibenzofuranyl group.

In one or more exemplary embodiments, the compound represented byFormula 201 or 202 may include at least one carbazole group.

In one or more exemplary embodiments, the compound represented byFormula 201 may not include a carbazole group.

In one or more exemplary embodiments, the compound represented byFormula 202 may be represented by Formula 201A-1 below:

In Formula 201A-1, L₂₀₃, xa3, and R₂₀₃ are the same as described above,and R₂₁₁ to R₁₂₆ may each independently be hydrogen, deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a phenyl group substitutedwith a C₁-C₁₀ alkyl group, a phenyl group substituted with —F, anaphthyl group, a phenanthrenyl group, an indenyl group, a fluorenylgroup, a dimethylfluorenyl group, a diphenylfluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, adimethylbenzofluorenyl group, a diphenylbenzofluorenyl group, anindenophenanthrenyl group, a dimethylindenophenanthrenyl group, adiphenylindenophenanthrenyl group, a pyridinyl group, a pyrrolyl group,a thiophenyl group, a furanyl group, an indolyl group, a phenylindolylgroup, a benzoindolyl group, a phenylbenzoindolyl group, an isoindolylgroup, a phenylindolyl group, a benzoisoindolyl group, aphenylbenzoisoindolyl group, a benzosilolyl group, adimethylbenzosilolyl group, a diphenylbenzosilolyl group, abenzothiophenyl group, a benzofuranyl group, a carbazolyl group, aphenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzosilolylgroup, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, adibenzothiophenyl group, and a dibenzofuranyl group.

The hole transport region may include one of HT1 to HT44,4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA),1-N,1-N-bis[4-(diphenylamino)phenyl]-4-N,4-N-diphenylbenzene-1,4-diamine(TDATA), 4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA),N,N′-di(naphtalene-1-yl)-N,N-diphenyl-benzidine (NPB or NPD),N4,N4′-di(naphthalen-2-yl)-N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(β-NPB),N,N′-bis(3-methylphenyl)-N,N-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD),4(N,N′-bis(3-methylphenyl)-N,N′-diphenyl-9,9-spirobifluorene-2,7-diamine(spiro-TPD), 2,7-bis[N-(1-naphthyl)anilino]-9,9′-spirobi[9H-fluorene](spiro-NPB),2,2′-dimethyl-N,N-di-[(1-naphthyl)-N,N-diphenyl]-1,1′-biphenyl-4,4′-diamine(methylated-NPB), 4,4′-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC),4,4′-bis[N,N-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD),4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combinationthereof, but the exemplary embodiments are not limited thereto.

The thickness of the hole transport region may be in a range of about100 Å to about 10,000 Å, and for example, about 100 Å to about 1,000 Å.When the hole transport region includes at least one selected from thehole injection layer and the hole transport layer, the thickness of thehole injection layer may be in a range of about 100 Å to about 9,000 Å,and for example, about 100 Å to about 1,000 Å, and the thickness of thehole transport layer may be in a range of about 50 Å to about 2,000 Å,and for example, about 100 Å to about 1,500 Å. When the thicknesses ofthe hole transport region, the hole injection layer, and the holetransport layer are within these ranges, satisfactory hole transportingcharacteristics may be obtained without a substantial increase indriving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for the optical resonance distance according to thewavelength of light emitted by the emission layer, and the electronblocking layer may block the flow of electrons from the electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

p-Dopant

The hole transport region may include, in addition to these materials, acharge-generation material for improvement of conductive properties. Thecharge-generation material may be homogeneously or non-homogeneouslydispersed in the hole transport region.

The charge-generation material may be, for example, a p-dopant.

In one or more exemplary embodiments, a LUMO energy level of thep-dopant may be about −3.5 eV or less.

The p-dopant may include a quinone derivative, a metal oxide, a cyanogroup-containing compound, or any combination thereof, but the exemplaryembodiments are not limited thereto.

In one or more exemplary embodiments, the p-dopant may include:

a quinone derivative such as tetracyanoquinodimethane TCNQ or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane F4-TCNQ;

a metal oxide such as tungsten oxide or molybdenum oxide;

a cyano group-containing compound such as1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile HAT-CN;

a compound represented by Formula 221; or

any combination thereof,

but the exemplary embodiments are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be a substituted or unsubstitutedC₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, or a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least one ofR₂₂₁ to R₂₂₃ may each independently be a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, or amonovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with: a cyano group; —F; —Cl; —Br; —I; a C₁-C₂₀ alkyl groupsubstituted with at least one cyano group; a C₁-C₂₀ alkyl groupsubstituted with at least one —F; a C₁-C₂₀ alkyl group substituted withat least one —Cl; a C₁-C₂₀ alkyl group substituted with at least one—Br; a C₁-C₂₀ alkyl group substituted with at least one —I; or anycombination thereof

Emission Layer in the Intermediate Layer 150

When the light-emitting device 10 is a full-color light-emitting device,the emission layer may be patterned into a red emission layer, a greenemission layer, and/or a blue emission layer, according to arepresentative sub-pixel. In one or more exemplary embodiments, theemission layer may have a stacked structure of two or more layersselected from the red emission layer, the green emission layer, and theblue emission layer, in which the two or more layers contact each otheror are separated from each other. In one or more exemplary embodiments,the emission layer may include two or more materials selected from a redlight-emitting material, a green light-emitting material, and a bluelight-emitting material, in which the two or more materials are mixedwith each other in a single layer to emit white light. In some exemplaryembodiments, the emission layer may be patterned or include a blueemission layer.

The emission layer may include a host and the dopant. The dopant mayinclude a phosphorescent dopant, a fluorescent dopant, or anycombination thereof.

In the emission layer, an amount of the dopant may be in a range ofabout 0.01 parts by weight to about 15 parts by weight based on 100parts by weight of the host, but the exemplary embodiments are notlimited thereto.

Alternatively, the emission layer may include a quantum dot.

The thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, and for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Host in Emission Layer

The host may include a compound represented by Formula 301:

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21)  <Formula 301>

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may be a substituted or unsubstituted C₃-C₁₀ cycloalkylene group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkylene group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, or a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group,

xb1 may be 0, 1, 2, 3, 4, or 5,

R₃₀₁ may be deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a substituted or unsubstituted C₁-C₆₀ alkyl group,a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), or —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be 1, 2, 3, 4, or 5, and

Q₃₀₁ to Q₃₀₃ are the same as described in connection with Q₁.

In one or more exemplary embodiments, when xb11 in Formula 301 is 2 ormore, two or more Ar₃₀₁(s) may be linked to each other via a singlebond.

In one or more exemplary embodiments, the host may include a compoundrepresented by Formula 301-1, a compound represented by Formula 301-2,or any combination thereof:

In Formulae 301-1 to 301-2,

ring A₃₀₁ to ring A₃₀₄ may each independently be a C₅-C₆₀ carbocyclicgroup or a C₁-C₆₀ heterocyclic group,

X₃₀₁ may be O, S, N-[(L₃₀₄)_(xb4)-R₃₀₄], C(R₃₀₄)(R₃₀₅), orSi(R₃₀₄)(R₃₀₅),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, and R₃₀₁ are the same as described above,

L₃₀₂ to L₃₀₄ are each independently the same as described in connectionwith L₃₀₁,

xb2 to xb4 are each independently the same as described in connectionwith xb1, and

R₃₀₂ to R₃₀₅ and R₃₁₁ to R₃₁₄ are the same as described in connectionwith R₃₀₁.

In one or more exemplary embodiments, the host may include an alkalineearth-metal complex. For example, the host may include a Be complex (forexample, Compound H55), a Mg complex, a Zn complex, or any combinationthereof.

In one or more exemplary embodiments, the host may include at least oneof Compounds H1 to H120, 9,10-Di(2-naphthyl)anthracene (ADN),2-Methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combinationthereof, but the exemplary embodiments are not limited thereto:

Phosphorescent Dopant Included in Emission Layer in Intermediate Layer150

The phosphorescent dopant may include at least one transition metal as acenter metal.

The phosphorescent dopant may include a monodentate ligand, a bidentateligand, a tridentate ligand, a tetradentate ligand, a pentadentateligand, a hexadentate ligand, or any combination thereof.

The phosphorescent dopant may be electrically neutral.

In one or more exemplary embodiments, the phosphorescent dopant mayinclude an organometallic compound represented by Formula 401:

In Formulae 401 and 402,

M may be a transition metal (for example, iridium (Ir), platinum (Pt),palladium (Pd), osmium (Os), titanium (Ti), gold (Au) hafnium (Hf),europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re) or thulium(Tm)),

L₄₀₁ may be a ligand represented by Formula 402, and xc1 may be 1, 2, or3, wherein, when xc1 is 2 or more, two or more L₄₀₁(s) may be identicalto or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein,when xc2 is two or more, two or more of L₄₀₂ may be identical to ordifferent from each other,

X₄₀₁ and X₄₀₂ may each independently be nitrogen or carbon,

A ring A₄₀₁ and a ring A₄₀₂ may each independently be a C₅-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group,

T₄₀₁ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)—*′,*—C(Q₄₁₁)(Q₄₁₂)—*′, *—C(Q₄₁₁)=C(Q₄₁₂)—*′, *—C(Q₄₁₁)=*′, or *═C(Q₄₁₁)=*′,

X₄₀₃ and X₄₀₄ may each independently be a chemical bond (for example, acovalent bond or a coordinate bond), O, S, N(Q₄₁₃), B(Q₄₁₃), P(Q₄₁₃),C(Q₄₁₃)(Q₄₁₄), or Si(Q₄₁₃)(Q₄₁₄),

Q₄₁₁ to Q₄₁₄ are the same as described in connection with Q₁,

R₄₀₁ and R₄₀₂ may each independently be hydrogen, deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, a substitutedor unsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstitutedC₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂),—B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), or —P(═O)(Q₄₀₁)(Q₄₀₂),

Q₄₀₁ to Q₄₀₃ are the same as described in connection with Q₁,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula401.

In one or more exemplary embodiments, in Formula 402, i) X₄₀₁ may benitrogen, and X₄₀₂ may be carbon, or ii) each of X₄₀₁ and X₄₀₂ may benitrogen.

In one or more exemplary embodiments, when xc1 in Formula 402 is 2 ormore, two rings A₄₀₁(s) in two or more L₄₀₁(s) may optionally linked toeach other via T₄₀₂, which is a linking group, or two rings A₄₀₂(s) mayoptionally linked to each other via T₄₀₃, which is a linking group (seeCompound PD1 to PD4 and PD7). T₄₀₂ and T₄₀₃ are the same as described inconnection with T₄₀₁.

L₄₀₂ in Formula 401 may be an organic ligand. In one or more exemplaryembodiments, L₄₀₂ may include a halogen group, a diketone group (forexample, a acetylacetonate group), a carboxylic acid group (for example,a picolinate group), —C(═O), a isonitrile group, a —CN group, aphosphorus group (for example, a phosphine group, a phosphite group, andthe like), or any combination thereof, but the exemplary embodiments arenot limited thereto.

The phosphorescent dopant may include, for example, a compound selectedfrom Compounds PD1 to PD25, or any combination thereof, but theexemplary embodiments are not limited thereto:

Fluorescent Dopant in the Emission Layer

The fluorescent dopant may include a compound of Formula 1, and theemission layer may be a fluorescent emission layer.

The fluorescent dopant may further include, for example, an arylaminecompound or a styrylamine compound, in addition to the compound ofFormula 1.

In one or more exemplary embodiments, the fluorescent dopant may furtherinclude a compound represented by Formula 501:

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be a substituted or unsubstitutedC₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, or a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be 0, 1, 2, or 3,

R₅₀₁ and R₅₀₂ may each independently be a substituted or unsubstitutedC₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, or a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be 1, 2, 3, 4, 5, or 6.

In one or more exemplary embodiments, Ar₅₀₁ in Formula 501 may be acondensed cyclic group in which three or more monocyclic groups arecondensed with each other (for example, an anthracene group, a chrysenegroup, a pyrene group, or the like).

In one or more exemplary embodiment, xd4 in Formula 501 may be 2, butthe exemplary embodiments are not limited thereto.

In one or more exemplary embodiments, the fluorescent dopant may includeone of Compounds FD1 to FD36, 4, 4′-bis(2,2′-diphenylethenyl)-biphenyl(DPVBi), 4,4′-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), or anycombination thereof:

Electron Transport Region in Intermediate Layer 150

The electron transport region may have i) a single layer structureconsisting of a single layer consisting of a single material, ii) asingle layer structure consisting of a single layer including aplurality of different materials, or iii) a multi-layered structureincluding a plurality of layers including a plurality of differentmaterials.

The electron transport region may include a buffer layer, a holeblocking layer, an electron control layer, an electron transport layer(ETL), an electron injection layer, or any combination thereof, but theexemplary embodiments are not limited thereto.

In one or more exemplary embodiments, the electron transport region mayhave an electron transport layer/electron injection layer structure, ahole blocking layer/electron transport layer/electron injection layerstructure, an electron control layer/electron transport layer/electroninjection layer structure, or a buffer layer/electron transportlayer/electron injection layer structure, wherein for each structure,constituting layers are sequentially stacked from the emission layer.However, exemplary embodiments of the structure of the electrontransport region are not limited thereto.

The electron transport region (for example, the buffer layer, the holeblocking layer, the electron control layer, or the electron transportlayer in the electron transport region) may include a metal-freecompound, capable of easily accepting electrons, including at least oneπ-electron-depleted nitrogen-containing cyclic group.

The “π-electron-depleted nitrogen-containing cyclic group” may be aC₁-C₆₀ heterocyclic group having at least one *—N═*′ moiety as aring-forming moiety.

In one or more exemplary embodiments, the “π-electron-depletednitrogen-containing cyclic group” may be i) a first ring, ii) acondensed cyclic group in which two or more first rings are condensedwith each other, or iii) a condensed cyclic group in which one or morefirst rings and one or more second rings are condensed with each other,wherein the first ring may be a heteromonocyclic group (for example, animidazole group, a pyridine group, or a triazine group) including atleast one *—N═*′ moiety as a ring-forming moiety, and the second ringmay be a cyclic group (for example, a benzene group, a dibenzofurangroup, or a carbazole group) excluding a *—N═*′ moiety as a ring-formingmoiety.

Examples of the π-electron-depleted nitrogen-containing cyclic groupinclude a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, a triazine group, a quinoline group, a benzoquinolinegroup, an isoquinoline group, a benzoisoquinoline group, a quinoxalinegroup, a benzoquinoxaline group, a quinazoline group, a benzoquinazolinegroup, a cinnoline group, a phenanthroline group, a phthalazine group, anaphthyridine group, an azacarbazole group, an azafluorene group, anazadibenzosilole group, an azadibenzothiophene group, an azadibenzofurangroup, a pyrazole group, an imidazole group, a triazole group, atetrazole group, an oxazole group, an isooxazole group, a thiazolegroup, an isothiazole group, an oxadiazole group, a thiadiazole group, abenzopyrazole group, a benzimidazole group, a benzoxazole group, abenzothiazole group, a benzoxadiazole group, a benzothiadiazole group,an imidazopyridine group, an imidazopyrimidine group, an imidazotriazinegroup, an imidazopyrazine group, and an imidazopyridazine group, but theexemplary embodiments are not limited thereto.

In one or more exemplary embodiments, the electron transport region mayinclude a compound represented by Formula 601 below and including atleast one π-electron-depleted nitrogen-containing cyclic group.

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21)  <Formula 601>

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be a substituted or unsubstituted C₃-C₁₀ cycloalkylene group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkylene group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, or a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group,

xe1 may be 0, 1, 2, 3, 4, or 5,

R₆₀₁ may be a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ are the same as described in connection with Q₁, and

xe21 may be 1, 2, 3, 4, or 5.

In one or more exemplary embodiments, at least one of Ar₆₀₁, L₆₀₁, andR₆₀₁ of Formula 601 may each independently include at least oneπ-electron-depleted nitrogen-containing ring.

In one or more exemplary embodiments, when xe11 in Formula 601 is 2 ormore, two or more Ar₆₀₁(s) may be linked to each other via a singlebond.

In one or more exemplary embodiments, Ar₆₀₁ in Formula 601 may be asubstituted or unsubstituted anthracene group.

In one or more exemplary embodiments, the electron transport region mayinclude a compound represented by Formula 601-1 below:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ are the same as described in connection with L₆₀₁,

xe611 to xe613 are the same as described in connection with xe1,

R₆₁₁ to R₆₁₃ are the same as described in connection with R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be hydrogen, deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, or a naphthyl group.

In one or more exemplary embodiments, xe1 and xe611 to xe613 in Formulae601 and 601-1 may each independently be 0, 1, or 2.

The electron transport region may include one of Compounds ET1 to ET36,2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-Diphenyl-1,10-phenanthroline (Bphen),tris-(8-hydroxyquinoline)aluminum (Alq₃),bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum(BAlq), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole(TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or anycombination thereof, but the exemplary embodiments are not limitedthereto:

Thicknesses of the buffer layer, the hole blocking layer, and theelectron control layer may each be in a range of about 20 Å to about1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses ofthe buffer layer, the hole blocking layer, and the electron controllayer are within these ranges, the electron blocking layer may haveexcellent electron blocking characteristics or electron controlcharacteristics without a substantial increase in driving voltage.

The thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangedescribed above, the electron transport layer may have satisfactoryelectron transport characteristics without a substantial increase indriving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include alkali metal complex, alkalineearth metal complex, or any combination thereof. A metal ion of thealkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or aCs ion, and a metal ion of the alkaline earth metal complex may be a Beion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinatedwith the metal ion of the alkali metal complex or the alkalineearth-metal complex may be a hydroxy quinoline, a hydroxy isoquinoline,a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine,a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxydiphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxyphenylpyridine, a hydroxy phenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene,or any combination thereof, but the exemplary embodiments are notlimited thereto.

In one or more exemplary embodiments, the metal-containing material mayinclude a Li complex. The Li complex may include, for example, CompoundET-D1 (lithium quinolate, LiQ) or ET-D2.

The electron transport region may include the electron injection layerthat facilitates the flow of electrons from the second electrode 190.The electron injection layer may directly contact the second electrode190.

The electron injection layer may have i) a single layer structureconsisting of a single layer consisting of a single material, ii) asingle layer structure consisting of a single layer including aplurality of different materials, or iii) a multi-layered structurehaving a plurality of layers including a plurality of differentmaterials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal-containing compound, analkaline earth-metal-containing compound, a rare earth metal-containingcompound, an alkali metal complex, an alkaline earth-metal complex, arare earth metal complex, or any combinations thereof.

The alkali metal may include Li, Na, K, Rb, Cs, or any combinationthereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or anycombination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb,Gd, or any combination thereof.

The alkali metal-containing compound, the alkaline earthmetal-containing compound, and the rare earth metal-containing compoundmay include oxides, halides (for example, fluorides, chlorides,bromides, or iodides), or any combination thereof, of the alkali metal,the alkaline earth metal, and the rare earth metal, respectively.

The alkali metal-containing compound may include alkali metal oxidessuch as Li₂O, Cs₂O, or K₂O, alkali metal halides such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI, or any combination thereof. The alkaline earthmetal-containing compound may include an alkaline earth metal compoundsuch as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1), or Ba_(x)Ca_(1-x)O(0<x<1). The rare earth metal-containing compound may include YbF₃,ScF₃, ScO₃, Y₂O₃, Ce₂O₃, GdF₃, TbF₃, YbI₃, ScI₃, TbI₃, or anycombination thereof.

The alkali metal complex, the alkaline earth metal complex, and the rareearth metal complex may include i) one of the alkali metal, the alkalineearth metal, and rare earth metal ions, and ii) a ligand combined withthe metal ion, for example, a hydroxy quinoline, a hydroxy isoquinoline,a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine,a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxydiphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxyphenylpyridine, a hydroxy phenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene,or any combination thereof, but the exemplary embodiments are notlimited thereto.

The electron injection layer may consist of an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal-containing compound, analkaline earth-metal-containing compound, a rare earth metal-containingcompound, an alkali metal complex, an alkaline earth-metal complex, arare earth metal complex, or any combinations thereof, as describedabove. In one or more exemplary embodiments, the electron injectionlayer may further include an organic material (for example, a compoundrepresented by Formula 601). When the electron injection layer furtherincludes an organic material, an alkali metal, an alkaline earth metal,a rare earth metal, an alkali metal-containing compound, an alkalineearth-metal-containing compound, a rare earth metal-containing compound,an alkali metal complex, an alkaline earth-metal complex, a rare earthmetal complex, or any combination thereof may be homogeneously ornon-homogeneously dispersed in a matrix including the organic material.

The thickness of the electron injection layer may be in a range of about1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have satisfactory electroninjection characteristics without a substantial increase in drivingvoltage.

Second Electrode 190

The second electrode 190 may be disposed on the intermediate layer 150having such a structure. The second electrode 190 may be a cathode whichis an electron injection electrode, and in this regard, a material forforming the second electrode 190 may be selected from a metal, an alloy,an electrically conductive compound, or a combination thereof, whichhave a relatively low work function.

The second electrode 190 may include lithium (Li), silver (Ag),magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, IZO, or anycombination thereof, but the exemplary embodiments are not limitedthereto. The second electrode 190 may be a transmissive electrode, asemi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Capping Layer

A first capping layer may be disposed outside the first electrode 110,and/or a second capping layer may be disposed outside the secondelectrode 190. In detail, the light-emitting device 10 may have astructure in which the first capping layer, the first electrode 110, theintermediate layer 150, and the second electrode 190 are sequentiallystacked, a structure in which the first electrode 110, the intermediatelayer 150, the second electrode 190, and the second capping layer aresequentially stacked, or a structure in which the first capping layer,the first electrode 110, the intermediate layer 150, the secondelectrode 190, and the second capping layer are sequentially stacked.

In the intermediate layer 150 of the light-emitting device 10, lightgenerated in the emission layer may pass through the first electrode 110and the first capping layer toward the outside, wherein the firstelectrode 110 may be a semi-transmissive electrode or a transmissiveelectrode. In the intermediate layer 150 of the light-emitting device10, light generated in the emission layer may pass through the secondelectrode 190 and the second capping layer toward the outside, whereinthe second electrode 190 may be a semi-transmissive electrode or atransmissive electrode.

The first capping layer and the second capping layer may increaseexternal luminescence efficiency according to the principle ofconstructive interference.

The first capping layer and the second capping layer may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one of the first capping layer and the second capping layer mayeach independently include a carbocyclic compound, a heterocycliccompound, an amine group-containing compound, a porphyrine derivative, aphthalocyanine derivative, a naphthalocyanine derivative, an alkalimetal complex, an alkaline earth metal complex, or any combinationthereof. The carbocyclic compound, the heterocyclic compound, and theamine group-containing compound may be optionally substituted with asubstituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combinationthereof.

In one or more exemplary embodiments, at least one of the first cappinglayer and the second capping layer may each independently include theamine group-containing compound.

In one or more exemplary embodiments, at least one of the first cappinglayer and the second capping layer may each independently include acompound selected from Compounds HT28 to HT33, a compound selected fromCompounds CP1 to CP5, or any compound thereof, but the exemplaryembodiments are not limited thereto:

Apparatus

The light-emitting device 10 may be included in at least one apparatus.For example, a light-emitting apparatus, an authentication apparatus, oran electronic apparatus may include the light-emitting device.

The light-emitting apparatus may further include a color filter, inaddition to the light-emitting device. The color filter may be locatedon at least one traveling direction of light emitted from thelight-emitting device. In one or more exemplary embodiments, lightemitted from the light-emitting device may be a blue light, but theexemplary embodiments are not limited thereto. The light-emitting devicemay be understood by referring to the description thereof providedherein.

The light-emitting apparatus may include a first substrate. The firstsubstrate may include a plurality of subpixel areas, and the colorfilter may include a plurality of color filter areas respectivelycorresponding to the plurality of the subpixel areas.

A pixel-defining film may be disposed between the plurality of thesubpixel areas to define each of the subpixel areas.

The color filter may further include light blocking patterns disposedbetween the plurality of the color filter areas.

The plurality of color filter areas may include a first color filterarea emitting first color light, a second color filter area emittingsecond color light, and/or a third color filter area emitting thirdcolor light, and the first color light, the second color light, and/orthe third color light may have different maximum emission wavelengthsfrom one another. For example, the first color light may be a red light,the second color light may be a green light, and the third color lightmay be a blue light, but the exemplary embodiments are not limitedthereto. In one or more exemplary embodiments, each of the plurality ofcolor filter areas may include a quantum dot, but the exemplaryembodiments are not limited thereto. In detail, the first color filterarea may include a red quantum dot, the second color filter area mayinclude a green quantum dot, and the third color filter area may notinclude a quantum dot. A quantum dot may be understood by referring tothe description thereof provided herein. Each of the first color filterarea, the second color filter area, and/or the third color filter areamay further include a scatterer, but the exemplary embodiments are notlimited thereto.

In one or more exemplary embodiments, the light-emitting device may emitfirst light, the first color filter area may absorb the first light toemit first first-color light, the second color filter area may absorbthe first light to emit second first-color light, and the third colorfilter area may absorb the first light to emit third first-color light.In this case, the first first-color light, the second first-color light,and the third first-color light may have different maximum emissionwavelengths from one another. In detail, the first light may be bluelight, the first first-color light may be red light, the secondfirst-color light may be green light, and the third first-color lightmay be blue light, but the exemplary embodiments are not limitedthereto.

The light-emitting apparatus may further include a thin-film transistor,in addition to the light-emitting device 10 as described above. Thethin-film transistor may include a source electrode, an activationlayer, and a drain electrode, and one of the source electrode and thedrain electrode may be electrically connected to the one of the firstelectrode 110 and the second electrode 190 of the light-emitting device10.

The thin-film transistor may further include a gate electrode, a gateinsulation film, or the like.

The activation layer may include a crystalline silicon, an amorphoussilicon, an organic semiconductor, an oxide semiconductor, or the like,but the exemplary embodiments are not limited thereto.

The light-emitting apparatus may further include a sealing part forsealing the light-emitting device 10. The sealing part may be disposedbetween the color filter and the light-emitting device 10. The sealingpart may allow light from the light-emitting device 10 to be outputtoward the outside and may block outside air and moisture frompenetrating into the light-emitting device 10. The sealing part may be asealing substrate including a transparent glass substrate or a plasticsubstrate. The sealing part may be a thin film encapsulation layerincluding a plurality of organic layers and/or a plurality of inorganiclayers. When the sealing part is a thin-film encapsulation layer, thelight-emitting apparatus may be flexible.

The light-emitting apparatus may be used as various displays, lightsources, and the like.

The authentication apparatus may be, for example, a biometricauthentication apparatus for authenticating an individual by usingbiometric information of a biometric body (for example, a finger tip, apupil, or the like).

The authentication apparatus may further include, in addition to thelight-emitting device as described above, a biometric informationcollector.

The electronic apparatus may be applied to personal computers (forexample, a mobile personal computer), mobile phones, digital cameras,electronic organizers, electronic dictionaries, electronic gamemachines, medical instruments (for example, electronic thermometers,sphygmomanometers, blood glucose meters, pulse measurement devices,pulse wave measurement devices, electrocardiogram (ECG) displays,ultrasonic diagnostic devices, or endoscope displays), fish finders,various measuring instruments, meters (for example, meters for avehicle, an aircraft, and a vessel), projectors, and the like, but theexemplary embodiments are not limited thereto.

Preparation Method

Layers constituting the hole transport region, an emission layer, andlayers constituting the electron transport region may be formed in acertain region by using one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, the emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec by taking into account the material formed into theformed layer and its structure.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2,000 rpm to about 5,000 rpm and at a heat treatment temperature ofabout 80° C. to about 200° C. by taking into account a material to beincluded in a layer to be formed, and the structure of a layer to beformed.

General Definition of Substituents

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, asec-butyl group, an isobutyl group, a tert-butyl group, an n-pentylgroup, a tert-pentyl group, a neopentyl group, an isopentyl group, asec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexylgroup, an isohexyl group, a sec-hexyl group, a tert-hexyl group, ann-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptylgroup, an n-octyl group, an isooctyl group, a sec-octyl group, atert-octyl group, an n-nonyl group, an isononyl group, a sec-nonylgroup, a tert-nonyl group, an n-decyl group, an isodecyl group, asec-decyl group, and a tert-decyl group. The term “C₁-C₆₀ alkylenegroup” as used herein refers to a divalent group having a structurecorresponding to the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a monovalenthydrocarbon group having at least one carbon-carbon double bond in themiddle or at the terminus of a C₂-C₆₀ alkyl group, and examples thereofinclude an ethenyl group, a propenyl group, and a butenyl group. Theterm “C₂-C₆₀ alkenylene group” as used herein refers to a divalent grouphaving a structure corresponding to the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” refers to a monovalent hydrogen grouphaving at least one carbon-carbon triple bond in the middle or at theterminus of a C₂-C₆₀ alkyl group, and examples thereof include a ethynylgroup and a propynyl group. The term “C₂-C₆₀ alkynylene group” as usedherein refers to a divalent group having a structure corresponding tothe C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by-OA₁₀₁ (wherein, A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon cyclic group having 3 to 10 carbon atoms, andexamples thereof include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctylgroup, an adamantanyl group, a norbornanyl group, a bicyclo[1.1.1]pentylgroup, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, and abicyclo[2.2.2]octyl group. The term “C₃-C₁₀ cycloalkylene group” as usedherein refers to a divalent group having a structure corresponding tothe C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent cyclic group having a heteroatom (for example, N, O, Si, P,S, or any combination thereof) as a ring-forming atom and 1 to 10 carbonatoms, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having a structure corresponding to the C₁-C₁₀ heterocycloalkylgroup.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent cyclic group that has 3 to 10 carbon atoms, at least onecarbon-carbon double bond in the ring thereof, and no aromaticity, andexamples thereof include a cyclopentenyl group, a cyclohexenyl group,and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylene group” asused herein refers to a divalent group having a structure correspondingto the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent cyclic group that has a heteroatom (for example, N, O, Si, P,S, or any combination thereof) as a ring-forming atom, 1 to 10 carbonatoms, and at least one double bond in its ring. Non-limiting examplesof the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having a structurecorresponding to the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, and aC₆-C₆₀ arylene group used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Examples of theC₆-C₆₀ aryl group include a phenyl group, a pentalenyl group, a naphthylgroup, an azulenyl group, an indacenyl group, an acenaphthyl group, aphenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a heptalenyl group, anaphthacenyl group, a picenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, and an ovalenyl group. Whenthe C₆-C₆₀ aryl group and the C₆-C₆₀ arylene group each include two ormore rings, the two or more rings may be fused to each other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a heterocyclic aromatic system that has a heteroatom (forexample, N, O, Si, P, S, or any combination thereof) as a ring-formingatom, in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having aheterocyclic aromatic system that has a heteroatom (for example, N, O,Si, P, S, or any combination thereof) as a ring-forming atom, inaddition to 1 to 60 carbon atoms. Examples of the C₁-C₆₀ heteroarylgroup include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group,a pyridazinyl group, a triazinyl group, a quinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinylgroup, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinylgroup, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinylgroup, a phthalazinyl group, and a naphthyridinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀ heteroarylene group each include two ormore rings, the rings may be fused with each other.

The term “C₆-C₆₀ aryloxy group” as used herein refers to-OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group used hereinindicates-SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic fused polycyclic group” as used hereinrefers to a monovalent group (for example, having 8 to 60 carbon atoms)having two or more rings fused with each other, only carbon atoms asring-forming atoms, and non-aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic fused polycyclicgroup include an indenyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, an indenophenanthrenyl group, and anindenoanthracenyl group. The term “divalent non-aromatic fusedpolycyclic group” as used herein refers to a divalent group having astructure corresponding to the monovalent non-aromatic fused polycyclicgroup.

A monovalent non-aromatic fused heteropolycyclic group as used hereinrefers to a monovalent group (for example, having 1 to 60 carbon atoms)having two or more rings fused with each other, a heteroatom (forexample, N, O, Si, P, S, or any combination thereof), in addition tocarbon atoms, as a ring-forming atom, and non-aromaticity in its entiremolecular structure. Examples of the monovalent non-aromatic fusedheteropolycyclic group include a pyrrolyl group, a thiophenyl group, afuranyl group, an indolyl group, a benzoindolyl group, a naphthoindolylgroup, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolylgroup, a benzosilolyl group, a benzothiophenyl group, a benzofuranylgroup, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenylgroup, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenylgroup, an azadibenzosilolyl group, an azadibenzothiophenyl group, anazadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, atriazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolylgroup, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, athiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, abenzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, abenzothiadiazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinylgroup, an imidazopyridazinyl group, an indeno carbazolyl group, anindolocarbazolyl group, a benzofurocarbazolyl group, abenzothienocarbazolyl group, a benzosilolocarbazolyl group, abenzoindolocarbazolyl group, a benzocarbazolyl group, abenzonaphthofuranyl group, a benzonaphthothiophenyl group, abenzonaphtho silolyl group, a benzofurodibenzofuranyl group, abenzofurodibenzothiophenyl group, and a benzothienodibenzothiophenylgroup. The term “divalent non-aromatic fused heteropolycyclic group” asused herein refers to a divalent group having a structure correspondingto the monovalent non-aromatic fused heteropolycyclic group.

The term “C₅-C₆₀ carbocyclic group” as used herein refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms and onlycarbon as ring-forming atoms. The term “C₅-C₆₀ carbocyclic group” may bean aromatic carbocyclic group or a non-aromatic carbocyclic group. Theterm “C₅-C₆₀ carbocyclic group” may be a compound such as benzene, amonovalent group such as a phenyl group, or a divalent group such as aphenylene group. Alternatively, depending on the number of substituentsconnected to the C₅-C₆₀ carbocyclic group, the C₅-C₆₀ carbocyclic groupmay be a trivalent group or a quadrivalent group.

Examples of C₅-C₆₀ carbocyclic group include a cyclopentadiene group, abenzene group, a pentalene group, a naphthalene group, an azulene group,an indacene group, an acenaphthylene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a perylene group,a pentaphene group, a heptalene group, a naphthacene group, a picenegroup, a hexacene group, a pentacene group, a rubicene group, a coronenegroup, an ovalene group, an indene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, an indeno phenanthrenegroup, and an indenoanthracene group.

The term “C₁-C₆₀ heterocyclic group” refers to a monocyclic orpolycyclic group having a heteroatom (for example, N, O, Si, P, S, orany combination thereof), in addition to carbon atoms (wherein, thecarbon atoms may number 1 to 60), as a ring-forming atom, and 1 to 60carbon atoms. The C₁-C₆₀ heterocyclic group may be an aromaticheterocyclic group or a non-aromatic heterocyclic group. The C₁-C₆₀heterocyclic group may be a compound such as pyridine, a monovalentgroup such as a pyridinyl group, or a divalent group such as apyridinylene group. Alternatively, depending on the number ofsubstituents connected to the C₁-C₆₀ heterocyclic group, the C₁-C₆₀heterocyclic group may be a trivalent group or a quadrivalent group.

The terms “hydrogen,” “deuterium,” “fluorine,” “chlorine,” “bromine,”and “iodine” refer to their respective atoms and corresponding radicals.

Examples of C₁-C₆₀ heterocyclic group include a pyridine group, apyrimidine group, a pyrazine group, a pyridazine group, a triazinegroup, a quinoline group, a benzoquinoline group, an isoquinoline group,a benzoisoquinoline group, a quinoxaline group, a benzoquinoxalinegroup, a quinazoline group, a benzoquinazoline group, a cinnoline group,a phenanthroline group, a phthalazine group, a naphthyridine group, apyrrole group, a thiophene group, a furan group, an indole group, abenzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, abenzothiophene group, a benzofuran group, a carbazole group, adibenzosilole group, a dibenzothiophene group, a dibenzofuran group, anazacarbazole group, an azafluorene group, an azadibenzosilole group, anazadibenzothiophene group, an azadibenzofuran group, a pyrazole group,an imidazole group, a triazole group, a tetrazole group, an oxazolegroup, an isoxazole group, a thiazole group, an isothiazole group, anoxadiazole group, a thiadiazole group, a benzopyrazole group, abenzimidazole group, a benzoxazole group, a benzothiazole group, abenzoxadiazole group, a benzothiadiazole group, an imidazopyridinegroup, an imidazopyrimidine group, an imidazotriazine group, animidazopyrazine group, an imidazopyridazine group, an indenocarbazolegroup, an indolocarbazole group, a benzofurocarbazole group, abenzothienocarbazole group, a benzosilolocarbazole group, abenzoindolocarbazole group, a benzocarbazole group, a benzonaphthofurangroup, a benzonaphthothiophene group, a benzonaphthosilole group, abenzofurodibenzofuran group, a benzofurodibenzothiophene group, and abenzothienodibenzothiophene group.

The substituted C₅-C₆₀ carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₁-C₆₀ alkylene group, thesubstituted C₂-C₆₀ alkenylene group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic fused polycyclic group, the substituted divalentnon-aromatic fused heteropolycyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic fused polycyclic group, and the substituted monovalentnon-aromatic fused heteropolycyclic group, as used herein, may be:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or anitro group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each substituted with at least one of deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic fused polycyclic group, amonovalent non-aromatic fused heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic fused polycyclic group, or amonovalent non-aromatic fused heteropolycyclic group, each substitutedwith at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic fused polycyclic group, a monovalentnon-aromatic fused heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(O₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂);

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂); or

any combination thereof.

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃, as used herein, mayeach independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic fused polycyclic group, amonovalent non-aromatic fused heteropolycyclic group, a biphenyl group,or a terphenyl group.

The term “Ph” as used herein refers to a phenyl group, the term “Me” asused herein refers to a methyl group, the term “Et” as used hereinrefers to an ethyl group, the term “ter-Bu” or “Bu^(t)” as used hereinrefers to a tert-butyl group, and the term “OMe” as used herein refersto a methoxy group.

The term “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group”. In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group” as used herein refers to “a phenyl groupsubstituted with a biphenyl group”. In other words, the “terphenylgroup” is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group.

* and *′, as used herein, unless defined otherwise, each refer to abinding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to exemplary embodiments and alight-emitting device according to exemplary embodiments will bedescribed in detail with reference to Synthesis Examples and Examples.The wording “B was used instead of A” used in describing SynthesisExamples refers to that an identical molar equivalent of B was used inplace of A.

EXAMPLES Synthesis Example: Synthesis of Compound

Synthesis Example 1

Synthesis of Intermediate 7-2

Intermediate 7-1 (1 eq), aniline (3eq),tris(dibenzylideneacetone)dipalladium(0) (0.1eq),tri-tert-butylphosphine (0.2eq), and sodium tert-butoxide (4eq) weredissolved in toluene, and then, were stirred at a temperature of 110° C.for 12 hours in a nitrogen atmosphere. The mixture was cooled andcleaned three times by using ethyl acetate and water, and then theobtained organic layer was dried by using MgSO₄ under reduced pressure.Column chromatography and recrystallization (dichloromethane:n-hexane)were performed thereon to obtain Intermediate 7-2. (Yield: 53%)

Synthesis of Intermediate 7-4

Intermediate 7-3 (1eq), 1,3-difluorobenzene (3eq), and cesium carbonate(3eq) were dissolved in N-methyl-2-pyrrolidone (NMP), and then, werestirred at a temperature of 190° C. for 12 hours in a nitrogenatmosphere. The mixture was cooled and dried under reduced pressure, andthen NMP was removed therefrom. Then, the remainder was cleaned threetimes by using ethyl acetate and water, and then the obtained organiclayer was dried by using MgSO₄ under reduced pressure. Columnchromatography was performed to obtain Intermediate 7-4. (Yield: 62%)

Synthesis of Intermediate 7-5

Intermediate 7-4 (1eq), Intermediate 7-2 (1eq),tris(dibenzylideneacetone)dipalladium(0) (0.1eq),tri-tert-butylphosphine (0.2eq), and sodium tert-butoxide (3eq) weredissolved in toluene, and then, were stirred at a temperature of 110° C.for 12 hours in a nitrogen atmosphere. The mixture was cooled, thencleaned three times by using ethyl acetate and water, and then theobtained organic layer was dried by using MgSO₄ under reduced pressure.Column chromatography and recrystallization (dichloromethane:n-hexane)were performed thereon to obtain Intermediate 7-5. (Yield: 77%)

Synthesis of Intermediate 7-6

Intermediate 7-5 (1 eq), tris(dibenzylideneacetone)dipalladium(0)(0.1eq), tri-tert-butylphosphine (0.2eq), and sodium tert-butoxide (3eq)were dissolved in toluene, and then, were stirred at a temperature of110° C. for 24 hours in a nitrogen atmosphere. The mixture was cooled,then cleaned three times by using ethyl acetate and water, and then theobtained organic layer was dried by using MgSO₄ under reduced pressure.Column chromatography and recrystallization (dichloromethane:n-hexane)were performed thereon to obtain Intermediate 7-6. (Yield: 42%)

Synthesis of Compound 7

Intermediate 7-6 (1 eq) was dissolved in ortho dichlorobenzene, and thenthe flask was cooled to a temperature of 0° C. in a nitrogen atmosphere,and then, BBr₃ (4 eq) was slowly added thereto. After completion of theaddition, the temperature was raised to 190° C. and the mixture wasstirred for 24 hours. After cooling to 0° C., triethylamine was slowlyadded into the flask until heating was stopped to terminate thereaction, and then, hexane was added thereto and the solid was filteredout. The obtained solid was purified by silica filtration and thenpurified by methylene chloride (CH₂Cl₂)/n-hexane (MC/Hex)recrystallization to obtain Compound 7. Then, sublimation purificationwas used for final purification. (Yield after sublimation: 4%)

Synthesis Example 2

Synthesis of Intermediate 10-2

Intermediate 10-1 (1eq), 3-fluoro-N-phenylaniline (1 eq),tris(dibenzylideneacetone)dipalladium(0) (0.1eq),tri-tert-butylphosphine (0.2eq), and sodium tert-butoxide (3eq) weredissolved in toluene, and then, were stirred at a temperature of 90° C.for 8 hours in a nitrogen atmosphere. The mixture was cooled, thencleaned three times by using ethyl acetate and water, and then theobtained organic layer was dried by using MgSO₄ under reduced pressure.Column chromatography and recrystallization (dichloromethane:n-hexane)were performed thereon to obtain Intermediate 10-2. (Yield: 67%)

Synthesis of Intermediate 10-3

Intermediate 10-2 (1 eq), 3-bromo-5-(diphenylamino)phenol (1.2eq), andcesium carbonate (3eq) were dissolved in NMP, and then, were stirred ata temperature of 190° C. for 12 hours in a nitrogen atmosphere. Themixture was cooled and dried under reduced pressure, and then NMP wasremoved therefrom. Then, the remainder was cleaned three times by usingethyl acetate and water, and then the obtained organic layer was driedby using MgSO₄ under reduced pressure. Column chromatography wasperformed to obtain Intermediate 10-3. (Yield: 66%)

Synthesis of Intermediate 10-4

Intermediate 10-4 was obtained in the same manner as Intermediate 7-5.(Yield: 72%)

Synthesis of Intermediate 10-5

Intermediate 10-5 was obtained in the same manner as Intermediate 7-6.(Yield: 47%)

Synthesis of Compound 10

Compound 10 was obtained by using Intermediate 10-5 in the same manneras Compound 7. (Yield after sublimation: 3%)

Synthesis Example 3

Synthesis of Intermediate 13-2

Intermediate 13-1 (1eq), Intermediate 10-1 (2.2eq),tris(dibenzylideneacetone)dipalladium(0) (0.1eq), BINAP (0.2eq), andsodium tert-butoxide (3eq) were dissolved in toluene, and then, werestirred at a temperature of 90° C. for 24 hours in a nitrogenatmosphere. The mixture was cooled and cleaned three times by usingethyl acetate and water, and then the obtained organic layer was driedby using MgSO₄ under reduced pressure. Column chromatography andrecrystallization (dichloromethane:n-hexane) were performed thereon toobtain Intermediate 13-2. (Yield: 67%)

Synthesis of Intermediate 13-3

Intermediate 13-3 was obtained in the same manner as Intermediate 7-5.(Yield: 63%)

Synthesis of Intermediate 13-4

Intermediate 13-4 was obtained in the same manner as Intermediate 7-6.(Yield: 42%)

Synthesis of Compound 13

Compound 13 was obtained by using Intermediate 13-4 in the same manneras Compound 7. (Yield after sublimation: 8%)

Synthesis Example 4

Synthesis of Intermediate 15-1

Intermediate 15-1 was obtained in the same manner as Intermediate 13-2.(Yield: 77%)

Synthesis of Intermediate 15-2

Intermediate 15-2 was obtained in the same manner as Intermediate 7-5.(Yield: 68%)

Synthesis of Intermediate 15-3

Intermediate 15-3 was obtained in the same manner as Intermediate 7-6.(Yield: 37%)

Synthesis of Compound 15

Compound 15 was obtained by using Intermediate 15-3 in the same manneras Compound 7. (Yield after sublimation: 7%)

Synthesis Example 5

Synthesis of Intermediate 16-1

Intermediate 13-1 (1eq), Intermediate 7-3 (1eq),tris(dibenzylideneacetone)dipalladium(0) (0.1eq),tri-tert-butylphosphine (0.2eq), and sodium tert-butoxide (3eq) weredissolved in toluene, and then, were stirred at a temperature of 90° C.for 8 hours in a nitrogen atmosphere. The mixture was cooled, thencleaned three times by using ethyl acetate and water, and then theobtained organic layer was dried by using MgSO₄ under reduced pressure.Column chromatography and recrystallization (dichloromethane:n-hexane)were performed thereon to obtain Intermediate 16-1. (Yield: 61%)

Synthesis of Intermediate 16-2

Intermediate 16-1 (1eq), Intermediate 10-1 (1eq),tris(dibenzylideneacetone)dipalladium(0) (0.1eq),tri-tert-butylphosphine (0.2eq), and sodium tert-butoxide (3eq) weredissolved in toluene, and then, were stirred at a temperature of 90° C.for 8 hours in a nitrogen atmosphere. The mixture was cooled, thencleaned three times by using ethyl acetate and water, and then theobtained organic layer was dried by using MgSO₄ under reduced pressure.Column chromatography and recrystallization (dichloromethane:n-hexane)were performed thereon to obtain Intermediate 16-2. (Yield: 73%)

Synthesis of Intermediate 16-3

Intermediate 16-4 was obtained in the same manner as Intermediate 10-3.(Yield: 42%)

Synthesis of Intermediate 16-4

Intermediate 16-3 (1eq), aniline (1eq),tris(dibenzylideneacetone)dipalladium(0) (0.1eq),tri-tert-butylphosphine (0.2eq), and sodium tert-butoxide (3eq) weredissolved in toluene, and then, were stirred at a temperature of 100° C.for 6 hours in a nitrogen atmosphere. The mixture was cooled, thencleaned three times by using ethyl acetate and water, and then theobtained organic layer was dried by using MgSO₄ under reduced pressure.Column chromatography and recrystallization (dichloromethane:n-hexane)were performed thereon to obtain Intermediate 16-4. (Yield: 55%)

Synthesis of Intermediate 16-5

Intermediate 16-5 was obtained in the same manner as Intermediate 7-6.(Yield: 36%)

Synthesis of Compound 16

Compound 16 was obtained by using Intermediate 16-3 in the same manneras Compound 7. (Yield after sublimation: 4%)

Proton nuclear magnetic resonance (¹H NMR) and mass spectroscopy/fastatom bombardment (MS/FAB) of compounds synthesized according toSynthesis Examples are shown in Table 1.

Synthesis methods of compounds other than Compounds shown in Table 1 mayalso be easily recognized by those of ordinary skill in the art byreferring to the synthesis mechanisms and source materials describedabove.

TABLE 1 Com- MS/FAB pound 1H NMR (CDCl3 , 400 MHz) found calc.  7 10.52(1H, s), 9.53 (2H, d), 7.54-7.36 (8H, m),  960.71  960.70 7.34-7.16(16H, m), 7.15-7.02 (7H, m), 7.01-6.90 (4H, m), 6.82 (2H, d), 5.81 (2H,d) 10 10.47 (1H, s), 9.46 (2H, d), 7.57-7.41 (10H, m), 1035.82 1035.817.43-7.19 (19H, m), 7.18-6.92 (8H, m), 6.90-6.70 (3H, m), 6.68 (1H, s),5.87 (1H, s) 5.83 (2H, s) 13 10.57 (1H, s), 9.65 (2H, d), 7.62-7.47(14H, m), 1110.94 1110.94 7.40-7.12 (14H, m), 7.10-6.87 (13H, m), 6.80-6.72 (5H, m), 5.82 (1H, s), 5.75 (2H, s) 15 10.43 (1H, s), 9.45 (2H, d),7.60-7.42 (7H, m),  888.73  888.71 7.40-7.12 (8H, m), 7.10-6.87 (7H, m),6.92- 6.87 (4H, m), 6.02 (1H, s), 5.83 (2H, s), 1.32 (18H, s) 16 10.40(1H, s), 9.43 (2H, d), 7.59-7.43 (9H, m), 1035.82 1035.80 7.36-7.14(13H, m), 7.10-6.92 (6H, m), 6.90-6.72 (12H, m), 5.92 (1H, s), 5.77 (1H,s), 5.67 (2H, s)

Manufacture of Light-Emitting Device

Example 1

As an anode, a 15 Ω/cm² (1,200 Å) indium-tin oxide (ITO) glass substrateobtained from Corning, Inc. of Corning, N.Y. was cut to a size of 50mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water eachfor 5 minutes, and then cleaned by exposure to ultraviolet rays andozone for 30 minutes. Then, the ITO glass substrate was provided to avacuum deposition apparatus.

A known compound NPD was vacuum-deposited on the ITO glass substrate toform a hole injection layer having a thickness of 300 Å, and a holetransport compound TCTA was vacuum-deposited on the hole injection layerto form a hole transport layer having a thickness of 200 Å. A holetransport compound9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi) wasvacuum-deposited on the hole transport layer to a thickness of 100 Å.

mCP and Compound 7 were co-deposited thereon at a weight ratio of 99:1to form an emission layer having a thickness of 200 Å.

Subsequently, diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide (TSPO1)as an electron transport layer was formed to a thickness of 200 Å, andthen, 1,3,5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI) as anelectron injection compound was deposited thereon to a thickness of 300Å.

Alkali metal halide LiF was deposited thereon to form an electroninjection layer having a thickness of 10 Å, aluminum wasvacuum-deposited to a thickness of 3,000 Å (cathode) to form a LiF/AIelectrode, thereby completing the manufacture of a light-emittingdevice.

Example 2

A light-emitting device was manufactured in the same manner as inExample 1, except that Compound 10 was used instead of Compound 7 informing an emission layer.

Example 3

A light-emitting device was manufactured in the same manner as inExample 1, except that Compound 13 was used instead of Compound 7 informing an emission layer.

Example 4

A light-emitting device was manufactured in the same manner as inExample 1, except that Compound 15 was used instead of Compound 7 informing an emission layer.

Example 5

A light-emitting device was manufactured in the same manner as inExample 1, except that Compound 16 was used instead of Compound 7 informing an emission layer.

Comparative Example 1

A light-emitting device was manufactured in the same manner as inExample 1, except that a known Compound 3-20 was used instead ofCompound 7 in forming an emission layer.

Driving voltage, efficiency, and maximum quantum efficiency, and thelike, at a current density of 10 mA/cm², were measured in order toevaluate characteristics of each of the light-emitting devicemanufactured according to Examples 1 to 5 and Comparative Example 1.

The driving voltage and the current density of the light-emitting devicewere measured by using a source meter (Keithley Instruments, 2400 seriesby Tektronix, Inc., of Beaverton, Oreg.), and the maximum quantumefficiency was measured by using an external quantum efficiencymeasurement apparatus sold under the trade designation C9920-2-12 ofHamamatsu Photonics Inc. of Hamamatsu-city, Japan.

In the evaluation of the maximum quantum efficiency, a luminance/currentdensity was measured by using a luminance meter with calibratedwavelength sensitivity, and the maximum quantum efficiency wascalculated by assuming angular luminance distribution (Lambertian) witha postulated perfect reflecting diffuser.

TABLE 2 Maximum Driving Effic- quantum voltage iency efficiency EmissionExample Emission layer (V) (Cd/A) (%) color Example 1 Compound 7 5.024.5 22.9 Blue color Example 2 Compound 10 4.9 25.6 23.5 Blue colorExample 3 Compound 13 4.8 27.2 24.2 Blue color Example 4 Compound 15 5.021.2 20.7 Blue color Example 5 Compound 16 4.9 24.3 22.8 Blue colorComparative Compound 5.5 19.9 19.5 Blue color Example 1 3-20

From Table 2, it was confirmed that the light-emitting devices ofExamples 1 to 5 show excellent results compared to the light-emittingdevice of Comparative Example 1.

The compound of Formula 1 according to one or more exemplary embodimentsis structurally distinct by further activating multiple resonance andhas a high f value and a lower ΔE_(ST). Accordingly, when an emissionlayer of a light-emitting device includes the compound of Formula 1according to one or more exemplary embodiments, efficiency is increased.The compound of Formula 1 according to one or more exemplary embodimentsfunctions as a delayed fluorescence dopant.

Although certain exemplary embodiments and implementations have beendescribed herein, other embodiments and modifications will be apparentfrom this description. Accordingly, the inventive concepts are notlimited to such embodiments, but rather to the broader scope of theappended claims and various obvious modifications and equivalentarrangements as would be apparent to a person of ordinary skill in theart.

What is claimed is:
 1. A light-emitting device comprising: a firstelectrode; a second electrode facing the first electrode; and anintermediate layer disposed between the first electrode and the secondelectrode and comprising an emission layer, wherein the first electrodeand the second electrode each independently include at least oneselected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),magnesium-silver (Mg—Ag), indium tin oxide (ITO), zinc oxide (ZnO), tinoxide (SnO2) and indium zinc oxide (IZO), and the intermediate layercomprises the compound of Formula 1:

wherein, in Formula 1: Y is O, S, or Se; X1 is NR11, O, or S, X2 isNR12, O, or S, X3 is NR13, O, or S, and X4 is NR14, O, or S; l, m, n,and o are each, independently from one another, 0 or 1, and at least oneof l, m, n, and o is 1; R1 to R5 and R11 to R14 are each, independentlyfrom one another, hydrogen, deuterium, a substituted or unsubstitutedC1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group,a substituted or unsubstituted C2-C60 alkynyl group, a substituted orunsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkylgroup, a substituted or unsubstituted C3-C10 cycloalkenyl group, asubstituted or unsubstituted C1-C10 heterocycloalkenyl group, asubstituted or unsubstituted C6-C60 aryl group, a substituted orunsubstituted C6-C60 aryloxy group, a substituted or unsubstitutedC6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic fusedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticfused heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —P(Q1)(Q2),—C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2); a1, a2, a3, and a5 are each,independently from one another, 1, 2, or 3; a4 is 1 or 2; twoneighboring substituents of R1 to R5 and R11 to R14 are linked to eachother to form a ring, and at least one substituent of the substitutedC1-C60 alkyl group, the substituted C2-C60 alkenyl group, thesubstituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group,the substituted C3-C10 cycloalkyl group, the substituted C1-C10heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, thesubstituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 arylgroup, the substituted C6-C60 aryloxy group, the substituted C6-C60arylthio group, the substituted C1-C60 heteroaryl group, the substitutedmonovalent non-aromatic fused polycyclic group, and the substitutedmonovalent non-aromatic fused heteropolycyclic group is: deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, aC2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, ora C1-C60 alkoxy group, each, independently from one another, substitutedwith at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkylgroup, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, aC6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, aC1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclicgroup, a monovalent non-aromatic fused heteropolycyclic group,—Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and—P(═O)(Q11)(Q12); and a C3-C10 cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, aC6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalentnon-aromatic fused polycyclic group, or a monovalent non-aromatic fusedheteropolycyclic group, each, independently from one another, optionallysubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenylgroup, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, amonovalent non-aromatic fused polycyclic group, a monovalentnon-aromatic fused heteropolycyclic group, —Si(Q21)(Q22)(Q23),—N(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22);—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and—P(═O)(Q31)(Q32); wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 toQ33 are each, independently from one another, hydrogen, deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, aC2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, aC3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 arylgroup, a C1-C60 heteroaryl group, a monovalent non-aromatic fusedpolycyclic group, a monovalent non-aromatic fused heteropolycyclicgroup, a biphenyl group, or a terphenyl group.
 2. The organiclight-emitting device of claim 1, wherein 1 and m are
 1. 3. The organiclight-emitting device of claim 1, wherein l, m, and o are 1, and n is 0,or l, m, and n are 1, and o is
 0. 4. The organic light-emitting deviceof claim 1, wherein l, m, n, and o are
 1. 5. The organic light-emittingdevice of claim 1, wherein Y is O, and R1 to R5 and R11 to R14 are each,independently from one another, a substituted or unsubstituted C1-C60alkyl group, a substituted or unsubstituted C6-C60 aryl group, asubstituted or unsubstituted C1-C60 heteroaryl group, a substituted orunsubstituted monovalent non-aromatic fused polycyclic, or —N(Q1)(Q2);wherein, Q1 and Q2 have the same meanings as in claim
 1. 6. The organiclight-emitting device of claim 1, wherein R11 to R14 are each,independently from one another, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, or asubstituted or unsubstituted monovalent non-aromatic fused polycyclic.7. The organic light-emitting device of claim 1, wherein R11 to R14 areeach, independently from one another: a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a thiadiazolyl group, an oxadiazolyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, or an azacarbazolyl group, each, independentlyfrom one another, optionally substituted with at least one of deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C1-C20 alkylgroup, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a thiadiazolyl group, an oxadiazolyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an azacarbazolyl group, —Si(Q31)(Q32)(Q33),—N(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); whereinQ31 to Q33 have the same meanings as in claim
 1. 8. The organiclight-emitting device of claim 1, wherein R1 to R5 and R11 to R14 areeach, independently from one another, hydrogen, deuterium, a methylgroup, an ethyl group, a propyl group, an isobutyl group, a sec-butylgroup, a ter-butyl group, a pentyl group, an iso-amyl group, or a hexylgroup, or a group of Formula 2a or 2b:

wherein, in Formulae 2a to 2b, Z1 to Z3 are each, independently from oneanother, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a thiadiazolyl group, an oxadiazolyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, or an azacarbazolyl group, a33 is 1, 2, 3, 4,or 5, and * indicates a binding site to neighboring atom.
 9. The organiclight-emitting device of claim 1, wherein the compound of Formula 1 is acompound of Formula 2 or 3:

wherein, in Formulae 2 and 3, R1 to R5, X1, X2, and a1 to a5 have thesame meanings as in claim
 1. 10. The organic light-emitting device ofclaim 1, wherein the compound of Formula 1 is a compound of Formula 4 or5:

wherein, in Formulae 4 and 5, R1 to R5, X1, X2, X4, and a1 to a5 havethe same meanings as in claim
 1. 11. The organic light-emitting deviceof claim 1, the compound of Formula 1 is a compound of Formula 6 or 7:

wherein, in Formulae 6 and 7, R1 to R5, X1 to X4, and a1 to a5 have thesame meanings as in claim
 1. 12. The organic light-emitting device ofclaim 1, wherein the compound of Formula 1 is one of the compoundsbelow:


13. The light-emitting device of claim 1, wherein the first electrodecomprises an anode, the second electrode comprises a cathode, and theintermediate layer comprises: i) a hole transport region disposedbetween the first electrode and the emission layer and comprising a holeinjection layer, a hole transport layer, an emission auxiliary layer, anelectron blocking layer, or any combination thereof and ii) an electrontransport region disposed between the emission layer and the secondelectrode and comprising a hole blocking layer, an electron transportlayer, an electron injection layer, or any combination thereof.
 14. Thelight-emitting device of claim 1, wherein the emission layer comprisesthe compound.
 15. The light-emitting device of claim 1, wherein theemission layer comprises a fluorescent emission layer.
 16. Thelight-emitting device of claim 1, wherein the emission layer comprises adopant, and the dopant comprises the compound.
 17. The light-emittingdevice of claim 16, wherein the compound comprises a delayedfluorescence dopant.
 18. The light-emitting device of claim 1, whereinthe emission layer comprises a blue emission layer.
 19. An electronicapparatus comprising a thin-film transistor and the light-emittingdevice of claim 1, wherein the thin-film transistor comprises a sourceelectrode, a drain electrode, an activation layer, and a gate electrode,and the first electrode of the light-emitting device is electricallyconnected to one of the source electrode and the drain electrode of thethin-film transistor.